A cigar-smoking bird named Shoe and political caricatures have made Jeff MacNelly a newspaper favorite.

On those rare occasions when Jeff MacNelly descends from his Virginia hilltop home to lope down Chicago's Michigan Avenue or traipse around Washington, D.C., he looks for all the world like an oversized bumpkin touring the big city. Large feet slap the pavement, large hands jam into pockets, an unruly thatch of gray hair brushes his heavy eyebrows, and thick glasses slide down his nose, which is small compared with his lantern chin and jug ears. He is a walking, six-foot-five-inch caricature--a "nerd," he cheerfully concedes.

Beneath that awkward appearance, however, is one of the sharpest wits and finest artists in American editorial cartooning and on the comics page. With the Chicago Tribune as his flagship paper, MacNelly, 51, is a three-time winner of the Pulitzer Prize for political cartoons and twice the recipient of the National Cartoonists Society's Reuben Award (named in honor of the late Rube Goldberg) for his editorial cartoons and his comic strip, "Shoe," about the cigar-smoking bird editor of the Treetops Tattler Tribune and his avian associates.

"I think MacNelly's one of the most influential cartoonists of the last 30 years," says political and comic art historian Richard Samuel West, a Northampton, Massachusetts-based dealer in early American magazines."Many younger cartoonists became interested in cartooning because of the vitality of his work, and that's why most cartoonists regard him as a pivotal figure in political cartooning in the latter part of this century."

According to Kevin Kallaugher, himself an award-winning editorial cartoonist for The Sun in Baltimore and a former president of the Association of American Editorial Cartoonists, other cartoonists "are dazzled by [MacNelly's] artistry, enchanted by his wit, and astonished with his originality.

"I know, I am one of them," wrote Kallaugher, also the editorial cartoonist for the Economist in London, in a tribute accompanying a display of MacNelly's cartoons at Forte Dei Marmi in Tuscany, Italy, which was held in connection with MacNelly's receipt of the 1998 Graphica Internazionale award.

MacNelly's thrice-weekly editorial cartoons for the Chicago Tribune are syndicated to approximately 400 newspapers, and "Shoe" appears in nearly 1,000 papers. He admits that his double duty as a political and comic strip artist is "hellacious," yet it does not seem to have diminished his astounding reservoir of creativity: he also does weekly illustrations for humorist Dave Barry's newspaper column, writes and illustrates books periodically, produces extraordinary, lavishly colored comic paintings and prints, crafts bronze and wire sculptures occasionally, and even turns out finely detailed model wooden boats. And he tinkers with his small fleet of vintage automobiles: a 1929 Model A, a 1931 Chrysler rumble-seat roadster, two 1952 U.S. Army Jeeps, a 1954 Willys four-wheel drive and a 1959 DeSoto--the model for the rattletrap conveyance that Shoe's colleague, the Perfesser, is forever taking to the mechanic.

MacNelly's remarkable productivity at the drawing board and easel is amply rewarded. Between his Tribune salary, syndication proceeds, merchandizing of "Shoe"--which has been turned into books, greeting cards and other products--and his prints and paintings, he has become one of the most highly paid political cartoonists in the country. He acknowledges earning nearly $1 million a year.

"It's like making it in Polish zlotys," shrugs MacNelly. "I mean, all I know is I can put the card in the ATM machine and get 300 bucks out of it, and I put it in my jeans and walk around with it for weeks. And, you know, the only reason I run out of cash is 'cause Susie [his wife] says, 'I gotta go to the hairdresser, can I have $40?'"

While MacNelly could easily spend exorbitant amounts on expensive premium cigars, he doesn't--although he, like his creation Shoe, savors a good smoke. During the depths of the winter, he lives in a tiny cottage in Key West, Florida, where he has access to a wide variety of cigars. On rare occasions, he even is the recipient of a contraband Havana--with which, he confesses, he is only mildly impressed.

"I hesitate to say this. These friends of mine have risked confiscation and possible fines to bring me [Havana] cigars if they come through London or somewhere. And they are really nice smokes," MacNelly says. "But I gotta tell you, I have cigars in Key West that are, like, three-dollar cigars, that are wonderful. And I think also that's probably because Key West is, in itself, basically a humidor. You could almost keep the cigars out on the porch. They'd just be fine. So they're good, sort of gooey, nice smokes.

"I like the maduros usually down there. I get these kind of nice, run-of-the-mill cigars, and they're great. To me, they match up with the Cubans. I don't think, when I smoke a Cuban cigar, that I'm having some 80-year-old brandy or something. I think the Dominican cigars are every bit as good as the Cubans."

Although MacNelly prefers Ashton Churchills, he has difficulty finding them near his Virginia home; and down in Florida he says he is "always roaming around" among different cigar brands and types. "There are some Fuente cigars of various kinds that I like. It just depends. Every once in a while I switch off."

For MacNelly, smoking cigars combines pleasure with practicality. "Susie calls them my 'think sticks,' because usually friends always know that I'm at home and working because the return to the air conditioning system is right over my desk, so when I fire up a cigar, the rest of the house gets the cigar smell.

"To me, it's just relaxing. And if I really have a heavy day--like on Sunday, when I work pretty much straight through--I'll probably smoke three cigars a day. Half of it is to keep me awake through the endless comic strip drawings. It's not a social thing with me, you know. I like to say it's 'crowd control.' Fire up a cigar and everyone leaves. It's kind of nice."

Up at 6:30 each morning, MacNelly leaves the second-floor bedroom of what he calls his "beach-house-style" residence, which he built in 1989, and commutes "16 steps" to his studio. He strolls past dramatically artistic photographs of world leaders (Richard Nixon, Leonid Brezhnev, Fidel Castro, Anwar Sadat), taken over the years by his good friend, Pulitzer Prize-winning photographer David Hume Kennerly. He works in a cluttered but bright and airy room, with paintings stacked against walls that are covered with framed cartoons by present-day colleagues and cartooning luminaries of the past.

MacNelly scours newspapers and magazines, listens to what he calls "the hideous National Public Radio" for the first two hours of the day--and "if something's really happening, that awful MSNBC, where you have to listen to the same ads over and over again every three minutes." He then decides what subject to address in his political cartoons.

He produces one editorial cartoon on Tuesdays for Wednesday's newspapers; one on Thursdays for Friday's papers, and one on Fridays for Sunday's papers. He does the drawings on 8-inch-by-12-inch slick stock paper with a combination of brushes, ink-brush pens and ballpoints. He works swiftly, preferring to finish a drawing within two hours, provided the composition he has devised is not too complex. "If you spend any more time on it, you get too nitpicky. It's not a fresh drawing," he says.

Once the ink is dry, MacNelly dispatches the cartoon by computer to an Aspen, Colorado-based aide, Chris Cassatt, who forwards it to the Tribune, which distributes it to MacNelly's syndicate clients.

On Sundays, MacNelly spends most of the day working on at least a week's worth of "Shoe" drawings, including the colored Sunday page. On Mondays, he produces the illustrations for his buddy Dave Barry's column. On other days he turns out paintings or sculptures, works on his model boats, or tends to the 10 horses he and his wife keep on their 110-acre farm (along with three dogs and seven cats), set atop a 1,200-foot peak with spectacular views of Virginia's Blue Ridge Mountains.

It is an intense regimen that MacNelly has maintained for more than two decades--through an occasionally turbulent private life that has included four marriages and the tragedy of losing a 24-year-old son in a rock climbing accident in 1996.

Despite the personal upheavals, MacNelly somehow has remained at the top of his game, producing work that is among the best in the business. "He's the Michael Jordan of the profession," says Signe Wilkinson, the Pulitzer Prize-winning editorial cartoonist for the Philadelphia Daily News--and one of the few women to ply the political cartooning trade.

MacNelly has been popular ever since he launched his career as an editorial cartoonist in December 1970, achieving sudden success despite considerable anomalies. For example, he was--and still is--a conservative in a profession that produces and celebrates antiestablishment liberals.

MacNelly remains unsurprised by the appeal of his conservative viewpoint. Although he scorns the conservative and liberal tags, believing them largely to be meaningless, he says that for many years conservatives were considered "the establishment," ripe for ridicule by cartoonists. He always felt, however, that for a long time the "liberal Democratic apparatus was the establishment," while the conservatives "actually were the outs." Adopting the traditional cartoonists' role of gadfly, he could gleefully attack the "establishment" as he perceived it--and score a lot of points.

With conservatism now ascendant, he finds political cartooning a bit more challenging. "Yeah, it's harder playing defense. You don't score any points playing defense.

"It's not as much fun as it used to be. It's much more fun to be in this small guerrilla band in the bunker, kind of criticizing everything that goes on because you have no responsibility."

Although he is happy to see conservatism triumphant, MacNelly is displeased by the right wing's penchant for intrusive moralizing. "I have some very good, old conservative friends whom I disagree with on this, but I think where I've become a kind of libertarian is basically in letting folks alone. And that's where the disconnect is with me and a lot of conservatives, when they say, 'Gotta get rid of government, get government off of people's backs--but, by the way, what are you doing in your bedroom?' That doesn't make sense to me."

Regardless of who is in power, however, MacNelly is confident that they will supply him with enough "ridiculosities," as he calls the blunders of the mighty, to keep him busy. "No matter how crazy a scenario I come up with, the reality is always much worse." Interviewed at the height of l'affaire Lewinsky, MacNelly called this political era "really primo for political cartoonists."

MacNelly was born in Manhattan on September 17, 1947, and grew up in Queens and in the town of Cedarhurst on Long Island. His father, the late C. L. (Bud) MacNelly, was an artistically gifted advertising executive in New York who spent several years as publisher of the old weekly Saturday Evening Post in the early 1960s before quitting to devote himself to portrait painting. His portrait of the Rev. Billy Graham appeared on the Post's cover while he still was its publisher.

MacNelly's late mother, born Ruth Fox in Chicago, also was multitalented. Originally planning to be a concert pianist (and adept at painting as well), she left Wittenberg College in her junior year to earn a degree in journalism from the University of Toledo. During the Second World War, she was the chief assistant to popular New York society columnist Elsa Maxwell.

As a youngster, MacNelly was fascinated by the editorial cartoons he saw reprinted in the Sunday "Week in Review" section of The New York Times and elsewhere. He was particularly enthralled by the work of Bill Mauldin and Herbert L. Block. Mauldin, the youngest Pulitzer Prize-winning cartoonist ever, was cited at the age of 23 in 1945 for his "Willie and Joe" cartoons that portrayed GIs in the Second World War; he bagged another Pulitzer in 1959 while at the St. Louis Post-Dispatch, then joined the staff of the Chicago Sun-Times. Herb Block--the Washington Post's legendary "Herblock"--won the first of his three Pulitzers in 1942. Coiner of the term "McCarthyism"; decades-long scourge of Richard Nixon; the dean of liberal cartoonists, Block is in his 70th year as a political commentator, having begun drawing editorial cartoons for the Chicago Daily News in 1929.

"Mauldin was an inspiration to me when I was growing up," recalls MacNelly, "because like most kids I was into tanks and warfare and G.I. Joe and everything else, and he was the cartoonist of World War II. He was my hero. My mother gave me a collection of his stuff, and I was just in awe of him and Herblock."

(Today, Block generously expresses awe of MacNelly: "He is not only an outstanding cartoonist but a real original--in his ideas, in the way he presents them and in his remarkable drawing, which applies to his strip as well as to his editorial cartoons. Jeff can do more with birds than most cartoonists can do with people or animals. And he has the incredible ability to draw caricatures of each person in a group--from memory.")

MacNelly went to the prestigious Phillips Academy in Andover, Massachusetts, where he did not distinguish himself academically. At least during this period he learned how to smoke cigars.

"It's a long, tortured, hilarious story. I was hunting snakes in Central America when I was 14. It was bizarre." He explains that a childhood friend who was a pre-medical student at Harvard University had invited him to join in an exotic expedition to do research for Harvard's Museum of Comparative Zoology during the summer of 1962. "I remember being in Mexico and we stopped somewhere and there was this little bunch of cigars--they were tied with a string--and they cost like a dollar for 25 of these beauties. And I said, 'What the hell,' and I bought the cigars. And I think that's when I started smoking cigars. They were great."

After the Phillips Academy, MacNelly spent four years at the University of North Carolina in Chapel Hill without obtaining a degree. "Most kids took notes and doodled in the margins; I doodled and took notes in the margins," he says.